Leonardtown: History, Art, and Waterways

Leonardtown offers several distinct ways to plan a stay: historic homes, art and local shops, as well as activities on the water. Tudor Hall and the Old Jail offer a glimpse into the history of St. Mary’s County; the A&E District is known for art, studios, shops, and restaurants. McIntosh Run and Breton Bay, by contrast, focus on paddling opportunities. When choosing a hotel, you can consider whether culture, local offerings, or time on the water matters most for your trip.

Historic Homes and the Butterfly Trail

Tudor Hall is a Georgian mansion overlooking Breton Bay. It houses the St. Mary’s County Historical Society and is considered a significant 18th-century home in St. Mary’s County. Calling it an 18th-century home places it in a historical period, while “Georgian” describes its architectural character. Tudor Hall therefore offers two historical perspectives, in addition to its view of the bay.

The Old Jail was expanded in 1876 and served as the St. Mary’s County jail until 1942. Today, it is preserved as a museum and is one of Leonardtown’s best-known historic landmarks. Unlike Tudor Hall, its story centers on its use as a jail and its transformation into a museum. The Leonardtown Visitor Center is also located in the Old Jail Museum; visitors can begin the Leonardtown Butterfly Trail there.

The family-friendly Leonardtown Butterfly Trail highlights historic landmarks, outdoor spaces, local artwork, local shops, and other discoveries in Leonardtown. Its themes therefore extend beyond the history of the Old Jail to include art and local shops. If you begin the trail at the Visitor Center, the historic museum also serves as the starting point for this broader perspective on Leonardtown.

Art, Shops, and First Fridays

The Leonardtown A&E District includes the St. Mary’s Arts Council, art galleries, studios, shops, and restaurants. The district brings art and local offerings together under one theme. First Fridays in Leonardtown combine a chic artistic flair with the charm of Southern Maryland. While the district encompasses the associated venues and shops, First Fridays put a distinct emphasis on Leonardtown’s artistic atmosphere.

Another focus is horses: A Moment In Time offers a year-round riding lesson and horse-leasing program for all skill levels. Lessons and leasing are the focus here; the year-round schedule and stated range of skill levels can help you decide whether this activity suits your travel interests. This offering is therefore distinct in nature from both the historic sites and the art and water activities.

Paddling on McIntosh Run and Breton Bay

The Port of Leonardtown Winery Park has a canoe and kayak launch on McIntosh Run. A scenic three-mile waterway runs from McIntosh Run to Leonardtown Wharf. The launch and the route described are two specific points of reference for paddlers; the route is given with a length and destination.

The Patuxent Adventure Center offers kayak and paddleboard rentals at Leonardtown Wharf; you can rent kayaks at McIntosh Run. Kayak rentals are therefore available at both named locations, while paddleboard rentals are offered at the wharf. While paddling on McIntosh Run and Breton Bay, you may have the chance to see bald eagles, beavers, muskrats, herons, and occasionally river otters. The chance to observe wildlife adds a nature element to the route and rental information, without promising a sighting on every trip.

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